Here's The Tough Lesson About Hiring This CEO Learned After Starting A Company Out Of A Dorm Room

Casalena says he held off hiring far too long in the beginning. He tried to do everything himself which was extremely stressful. When he finally did start building a team, he didn't have any set of criteria for what would make a good hire versus a bad one. He didn't think hard about either group dynamics or communication.

This inexperience led to some hiring mistakes that ultimately held the team back.

Squarespace now employs about 380 people and was chosen as one of the best places to work for the last two years by Crain's New York.

Although Casalena still doesn't find hiring to be an easy process, he tells Business Insider that he now has a clear set of criteria about what makes someone a good fit for his company.

In interviews, the Squarespace team will ask a candidate questions about how they thought about problems in their past jobs to get an idea of their judgement.

"We try to figure out how detailed of a thinker people are in respect to decisions in their life," he says. "It's not a command-and-control sort of hierarchy here where we tell you every single thing to do. You have to be able to operate with really good judgement by yourself."

Casalena also says that he looks for good technologies who can communicate well and who have what he calls "intrinsic alignment." Squarespace looks for employees whose talents are deeply ingrained, and who firmly believe in where the company's mission.

"Like, if we're hiring an engineer, we're looking for someone who has loved making things since they were a kid," he says. "If you've been doing it since you were a kid, you're doing it because you like it. And we want to find people who are aligned with where we want to go."

Squarespace just announced a new software upgrade that gives users simplified site editing controls, integration with Getty Images and Google Apps for Work, and a whole bunch of new site templates. The company charges people or businesses as little as $8 a month to build and host websites. It raised a $40 million Series B in April.